WO2002022262A3 - Rhenium alkylidene catalysts fixed on a carrier and used for the metathesis of olefins - Google Patents

Rhenium alkylidene catalysts fixed on a carrier and used for the metathesis of olefins Download PDF

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Publication number
WO2002022262A3
WO2002022262A3 PCT/EP2001/010675 EP0110675W WO0222262A3 WO 2002022262 A3 WO2002022262 A3 WO 2002022262A3 EP 0110675 W EP0110675 W EP 0110675W WO 0222262 A3 WO0222262 A3 WO 0222262A3
Authority
WO
WIPO (PCT)
Prior art keywords
carrier
metathesis
olefins
catalyst
alkylidene catalysts
Prior art date
Application number
PCT/EP2001/010675
Other languages
German (de)
French (fr)
Other versions
WO2002022262A2 (en
Inventor
Jean-Marie Basset
Mathieu Chabanas
Christophe Coperet
Original Assignee
Basf Ag
Jean-Marie Basset
Mathieu Chabanas
Christophe Coperet
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Ag, Jean-Marie Basset, Mathieu Chabanas, Christophe Coperet filed Critical Basf Ag
Priority to JP2002526504A priority Critical patent/JP2004508191A/en
Priority to EP01976225A priority patent/EP1322418A2/en
Priority to CA002422594A priority patent/CA2422594A1/en
Priority to AU2001295565A priority patent/AU2001295565A1/en
Priority to US10/363,858 priority patent/US6878660B2/en
Publication of WO2002022262A2 publication Critical patent/WO2002022262A2/en
Publication of WO2002022262A3 publication Critical patent/WO2002022262A3/en

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
    • B01J31/1625—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts immobilised by covalent linkages, i.e. pendant complexes with optional linking groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
    • C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • B01J2231/74—Aziridination
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention relates to a novel, heterogeneous catalyst which is especially suitable for the metathesis of olefins, in addition to the production and corresponding use of the same. Said catalyst is fixed on an inorganic carrier and contains at least one active rhenium compound having at least one carbene group and optionally other functional groups. The rhenium compound is bonded to the material used as the carrier by a chemical bond. Preferably, a catalyst is used, which corresponds to formula (III) wherein S is a suitable carrier, preferably SiO2, and R?1, R2 and R3¿ independently represent a linear or branched C¿1?-C5 alkyl group, preferably a tert-butyl group.
PCT/EP2001/010675 2000-09-15 2001-09-14 Rhenium alkylidene catalysts fixed on a carrier and used for the metathesis of olefins WO2002022262A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2002526504A JP2004508191A (en) 2000-09-15 2001-09-14 Catalysts fixed on supports and their use for metathesis of olefins
EP01976225A EP1322418A2 (en) 2000-09-15 2001-09-14 Catalysts fixed on a carrier and used for the metathesis of olefins
CA002422594A CA2422594A1 (en) 2000-09-15 2001-09-14 Rhenium alkylidene catalysts fixed on a carrier and used for the metathesis of olefins
AU2001295565A AU2001295565A1 (en) 2000-09-15 2001-09-14 Rhenium alkylidene catalysts fixed on a carrier and used for the metathesis of olefins
US10/363,858 US6878660B2 (en) 2000-09-15 2001-09-14 Catalyst fixed on a carrier and used for the metathesis of olefins

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10046143A DE10046143A1 (en) 2000-09-15 2000-09-15 Supported catalysts for olefin metathesis
DE10046143.3 2000-09-15

Publications (2)

Publication Number Publication Date
WO2002022262A2 WO2002022262A2 (en) 2002-03-21
WO2002022262A3 true WO2002022262A3 (en) 2002-10-24

Family

ID=7656654

Family Applications (1)

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PCT/EP2001/010675 WO2002022262A2 (en) 2000-09-15 2001-09-14 Rhenium alkylidene catalysts fixed on a carrier and used for the metathesis of olefins

Country Status (9)

Country Link
US (1) US6878660B2 (en)
EP (1) EP1322418A2 (en)
JP (1) JP2004508191A (en)
CN (1) CN1457272A (en)
AU (1) AU2001295565A1 (en)
CA (1) CA2422594A1 (en)
DE (1) DE10046143A1 (en)
WO (1) WO2002022262A2 (en)
ZA (1) ZA200302067B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120289617A1 (en) * 2011-05-10 2012-11-15 Saudi Arabian Oil Company Hybrid Catalyst for Olefin Metathesis
DE102014105885A1 (en) * 2014-04-25 2015-10-29 Universität Stuttgart N-heterocyclic carbene complexes of metalimidoalkylidenes and metalloxoalkylidenes and their use
CN104311378B (en) * 2014-11-11 2016-02-24 万华化学集团股份有限公司 A kind of preparation method preparing neohexene and catalyzer thereof
WO2016207835A1 (en) 2015-06-25 2016-12-29 King Abdullah University Of Science And Technology Process for compound transformation

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2525224A1 (en) * 1982-04-14 1983-10-21 Rhone Poulenc Chim Base Carbene type transition metal complex coordinated with Lewis acid - used as catalyst for metathesis of simple or functionalised olefin(s)
US4818442A (en) * 1984-10-09 1989-04-04 Phillips Petroleum Company Disproportionation process
US5087710A (en) * 1990-01-04 1992-02-11 Massachusetts Institute Of Technology Homogeneous rhenium catalysts for metathesis of olefins
US5146033A (en) * 1990-01-04 1992-09-08 Massachusetts Institute Of Technology Homogeneous rhenium catalysts for metathesis of olefins
US5342985A (en) * 1988-12-10 1994-08-30 Hoechst Ag Organic derivatives of rhenium oxides and their preparation and use for the metathesis of olefins
WO1998002244A1 (en) * 1996-07-12 1998-01-22 Centre National De La Recherche Scientifique (Cnrs) Method of metathesis of alcanes and catalyst

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI84562C (en) * 1990-01-16 1991-12-27 Neste Oy FARING EQUIPMENT FOR THE FRAME STATION OF HETEROGENE CATALYSTATORS.
US5175311A (en) * 1990-03-29 1992-12-29 Research Corporation Technologies, Inc. Method of enantioselective cyclopropanation using chiral catalysts
US5198511A (en) * 1991-12-20 1993-03-30 Minnesota Mining And Manufacturing Company Polymerizable compositions containing olefin metathesis catalysts and cocatalysts, and methods of use therefor
JP3521912B2 (en) * 1993-12-30 2004-04-26 エクソンモービル・ケミカル・パテンツ・インク Method for synthesizing trans non-conjugated diolefin
BE1008339A3 (en) * 1994-05-03 1996-04-02 Dsm Nv Heterogeneous metathesis catalyst.
DE19932060A1 (en) * 1999-07-12 2001-01-18 Basf Ag Process for the production of C¶5¶ / C¶6¶ olefins

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2525224A1 (en) * 1982-04-14 1983-10-21 Rhone Poulenc Chim Base Carbene type transition metal complex coordinated with Lewis acid - used as catalyst for metathesis of simple or functionalised olefin(s)
US4818442A (en) * 1984-10-09 1989-04-04 Phillips Petroleum Company Disproportionation process
US5342985A (en) * 1988-12-10 1994-08-30 Hoechst Ag Organic derivatives of rhenium oxides and their preparation and use for the metathesis of olefins
US5087710A (en) * 1990-01-04 1992-02-11 Massachusetts Institute Of Technology Homogeneous rhenium catalysts for metathesis of olefins
US5146033A (en) * 1990-01-04 1992-09-08 Massachusetts Institute Of Technology Homogeneous rhenium catalysts for metathesis of olefins
WO1998002244A1 (en) * 1996-07-12 1998-01-22 Centre National De La Recherche Scientifique (Cnrs) Method of metathesis of alcanes and catalyst

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
BUFFON, R.; LECONTE, M.; CHOPLIN, A.; BASSET, J.M.: "Molecular Heterogenous Metathesis Catalysts: an Attempted Synthesis of Surface-anchored Alkylidenetungsten Complexes", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS, 1994, pages 1723 - 1729, XP001057094 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TOREKI, ROBERT ET AL: "A well-defined rhenium(VII) olefin metathesis catalyst", XP002191429, retrieved from STN Database accession no. 112:158626 CA *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TOREKI, ROBERT ET AL: "Metathetical reactions of rhenium(VII) alkylidene-alkylidyne complexes of the type Re(CR')(CHR')[OCMe(CF3)2]2 (R' = CMe3 or CMe2Ph) with terminal and internal olefins", XP002191428, retrieved from STN Database accession no. 118:124718 CA *
HERRMANN W A: "Essays on organometallic chemistry, VII. Laboratory curiosities of yesterday, catalysts of tomorrow: organometallic oxides", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 500, no. 1, 1 September 1995 (1995-09-01), pages 149 - 173, XP004023682, ISSN: 0022-328X *
HERRMANN, W.A.; WAGNER, W.; FLESSNER, U.N.; VOLKHARDT, U.; KOMBER, H.: "Methyltrioxorhenium as Catalyst for Olefin Metathesis", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION ENGLISH, vol. 30, no. 12, 1991, pages 1636 - 1638, XP002191427 *
HORTON, A.D.; SCHROCK, R.R.: "Preparation of Bis and Tris(arylimido) Complexes of Rhenium(VII), including Bis(arylimido) Neopentylidene Complexes, Candidates as Olefin Metathesis Catalysts", POLYHEDRON, vol. 7, no. 19/20, 1988, pages 1841 - 1853, XP002203232 *
J. AM. CHEM. SOC. (1990), 112(6), 2448-9, 1990 *
J. AM. CHEM. SOC. (1993), 115(1), 127-37, 1993 *
LAPOINTE, ANNE M. ET AL: "Alkyl, Alkylidene, and Alkylidyne Complexes of Rhenium", ORGANOMETALLICS (1995), 14(4), 1875-84, XP002203230 *
SCHEKLER-NAHAMA F ET AL: "Influence of Lewis acidity of rhenium heptoxide supported on alumina catalyst on the catalytic performances in olefin metathesis", APPLIED CATALYSIS A: GENERAL, ELSEVIER SCIENCE, AMSTERDAM, NL, vol. 167, no. 2, 27 February 1998 (1998-02-27), pages 237 - 245, XP004271398, ISSN: 0926-860X *
TOREKI, ROBERT ET AL: "Synthesis and characterization of rhenium(VII) alkylidene alkylidyne complexes of the type Re(CR')(CHR')(OR)2 and related species", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 114, no. 9, 1992, pages 3367 - 3380, XP002203231 *
WEISS, K.; LÖSSEL, G.: "Heterogenous, Metathesis-active Schrock-type Carbene Complexes by Reaction of Carbyne Tungsten(VI) Complexes with Silica Gel", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION ENGLISH, vol. 28, no. 1, 1989, pages 62 - 64, XP001061665 *

Also Published As

Publication number Publication date
CN1457272A (en) 2003-11-19
US20030181776A1 (en) 2003-09-25
DE10046143A1 (en) 2002-05-29
US6878660B2 (en) 2005-04-12
WO2002022262A2 (en) 2002-03-21
ZA200302067B (en) 2004-04-01
CA2422594A1 (en) 2003-03-14
AU2001295565A1 (en) 2002-03-26
EP1322418A2 (en) 2003-07-02
JP2004508191A (en) 2004-03-18

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